methyl(7R)-7-[beta-alanyl(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate → methyl(7R)-7-[(3-aminopropyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 421939Notes

Reaction equation

HRID 421939 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([N:6]([CH3:36])[C@@H:7]1[CH2:14][N:13]2[C:15]3[CH:16]=[C:17]([C:28]([O:30][CH3:31])=[O:29])[CH:18]=[CH:19][C:20]=3[C:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:12]2[C:11]2[CH:32]=[CH:33][CH:34]=[CH:35][C:10]=2[O:9][CH2:8]1)=O>C1COCC1>[NH2:1][CH2:2][CH2:3][CH2:4][N:6]([CH3:36])[C@@H:7]1[CH2:14][N:13]2[C:15]3[CH:16]=[C:17]([C:28]([O:30][CH3:31])=[O:29])[CH:18]=[CH:19][C:20]=3[C:21]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:12]2[C:11]2[CH:32]=[CH:33][CH:34]=[CH:35][C:10]=2[O:9][CH2:8]1

Participants

3

Reactant 1

HCID 66674855methyl(7R)-7-[beta-alanyl(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Product 1

HCID 66674629methyl(7R)-7-[(3-aminopropyl)(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl(7R)-7-[β-alanyl(methyl)amino]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.2 M) in THF was treated with BH3-DMS complex (2 M in THF; 10 eq.) and the resulting mixture was stirred for 3 h at RT. The reaction was quenched by the careful addition of HCl/MeOH (1.25 M) and the resulting solution refluxed for 2 h. The volatiles were then removed in vacuo and the residue partitioned between sat. aq. NaHCO3 and EtOAc. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The product was used directly in the next step without further purification. (ES+) m/z 476 (M+H)+.

Workup

  1. customThe reaction was quenched by the careful addition of HCl/MeOH (1.25 M)
  2. temperaturethe resulting solution refluxed for 2 h
  3. customThe volatiles were then removed in vacuo
  4. customthe residue partitioned between sat. aq. NaHCO3 and EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe product was used directly in the next step without further purification

Sources & evidence

ORD record
ord-996aa72290c44dce9c64c42fe7c25517
Source dataset
uspto-grants-2012_01
Patent number
US08101595B2

Reaction notes

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